Testing the Best Men’s Flip-Flops

Smothering your feet inside shoes and socks during the heat of summer is a strange form of self-torture. Set your dogs free with these five tried and true flip-flops for 2018, which range from stylish to damned-near orthopedic.

The Test

I put these through their paces for over two months of running errands, cruising around town, gardening, and hiking in the heat. They’ve plunged in creeks and taken long dusty walks on fire roads. I wore each pair for at least two three-mile walks. I also tested their mettle on a steep trail near my home in Ashland, Oregon, that rises nearly 200 feet in about an eighth of a mile.

The Results

(Sarah Jackson)

Most Comfortable: Keen Kona Flip II ($50)

The deeply sunken footbed and thick plush upper made this flip-flop by far the cushiest for both around-town duty and hiking. While not being as grippy as the Chaco’s, the siped sole was on par with the Filipe’s for descending trails. The Kona would have been slightly more trailworthy on the steep stuff if it had hugged the foot a little tighter, though that’d also rob it of some comfort. Note: if you prefer a tight next-to-foot feel, go a half-size down from your usual.

Classiest: OluKai Nohona Ulana ($85)

A blue woven upper and leather accents really give the Nohona a dash of style. You could almost wear a pair in the office on a casual summer Friday. The mildest tread of any of the flip-flops on this test didn’t do the Nohona any favors on steeper trails, but on flat ground, the supple leather toe post and subtly contoured footbed made for the second most comfortable flip on this list.

Most Versatile: Hari Mari Parks ($55)

While the footbed shows off all the style that gray hemp has to offer, the upper’s soft underside and the toe post’s cush memory-foam stuffing made the Parks remarkably comfortable, without any break-in time. The upper and footbed don’t boast any fancy tech details, but the deeply treaded outsole offered the grip of a performance-minded flip-flop on descents, which was a lot more than I expected from this a laid-back, surfer-style thong.

Best on Water: Astral Filipe ($75)

Shoemakers have been trying to make a river flip-flop for decades. The results have been disappointing, usually a wildly overbuilt sandal that no longer resembles a flip-flop. The Filipe stands out as the smartest and most successful effort to date. The secret is a piece of webbing that locks the top of your foot and heel down to the bed but that’s also removable when all you want is a simple thong. I thought the webbing would chafe but was pleasantly proved wrong on an eight-mile hike. Given how well it gripped my foot as I scurried down a steep trail, I’d expect the Felipe to stay in place if I took an unexpected swim on a rafting trip.

Best on Trail: Chaco Flip EcoTread ($65)

While the hard, textured footbed didn’t lend the EcoTread any comfort, the shoe did grip the bottom of my foot exceptionally well during steep climbs and descents. Couple that with a hearty toe post and upper, and the most deeply ridged outsole on this list, and you have a flip-flop that hikes almost like a boot. If you are a raft guide or work in an outdoor job where grip and performance are top priorities, the EcoTread is your best bet for flip-flops.